Styrene → HCID 19833160, compound

HRID 2051352Notes

Reaction equation

HRID 2051352 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1.[CH2:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]2[C:9](=[CH:8][CH:7]=1)[CH2:12][C:13](=[O:14])[CH2:16][CH:17]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7501StyreneHCID 906924-Chlorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19833160HCID 19833160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

8.00 g (0.06 mol) of aluminum chloride are suspended in 600 mI of methylene chloride, treated at 0° with 7.56 g (0.04 mol) of 4-chlorophenylacetyl chloride in 250 ml of methylene chloride and a solution of 4.17 g (0.04 mol) of styrene in 400 ml of methylene chloride is added dropwise thereto at -40° to -50° . After warming to room temperature, the mixture is poured on to ice, extracted with methylene chloride, dried with magnesium sulfate, filtered over Dicalit and the solvent is distilled in a vacuum. Chromatography on silica gel with ethyl acetatehexane (1:4) and recrystallization from ether/hexane gives 6-chloro-3,4-dihydro-4-phenyl-2(1H)-naphthalenone as beige crystals with melting point 61-62°.

Workup

  1. customat -40° to -50°
  2. additionthe mixture is poured on to ice
  3. extractionextracted with methylene chloride
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered over Dicalit
  6. distillationthe solvent is distilled in a vacuum
  7. customChromatography on silica gel with ethyl acetatehexane (1:4) and recrystallization from ether/hexane

Sources & evidence

ORD record
ord-948932159a434c1284b0aafa299572b1
Source dataset
uspto-grants-1991_05
Patent number
US05017608

Reaction notes

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